Acetone → HCID 53825815, compound

HRID 1493750Notes

Reaction equation

HRID 1493750 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH2:7]([C:9]1[C:17]2[O:16][CH2:15][O:14][C:13]=2[CH:12]=[CH:11][C:10]=1[CH2:18][C:19]([CH3:24])([CH3:23])C(O)=O)[CH3:8].C(N([CH2:30][CH3:31])CC)C.[N-:32]=[N+]=[N-].[Na+].[CH3:36][C:37]([CH3:39])=O>O>[CH2:7]([C:9]1[C:17]2[O:16][CH2:15][O:14][C:13]=2[CH:12]=[CH:11][C:10]=1[CH2:18][C:19]([NH:32][C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:31]=[CH:30][CH:39]=[CH:37][CH:36]=1)([CH3:23])[CH3:24])[CH3:8]

Participants

7

Reactant 5

HCID 180Acetone2×HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 14346541HCID 14346541, compound

Product 1

HCID 53825815HCID 53825815, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Ethyl chloroformate (1.87 g) in acetone (10 ml) was added to a stirred solution of the product from Stage (iv) (3.6 g) and triethylamine (1.58 g) in acetone (40 ml) and water (5 ml) at 5°. A solution of sodium azide (1.22 g) in water (10 ml) was added and the mixture was stirred for 30 min at 5°. The mixture was diluted with water and extracted with toluene. The extracts were dried, heated on a steam bath for 1 h and evaporated. The residue was heated in benzyl alcohol (21 ml) at 100° for 18 h. The mixture was then distilled in vacuo and purified by FCC using hexane/ether (7:3) as eluent to give the title compound as a colourless oil (4 g).

Workup

  1. extractionextracted with toluene
  2. customThe extracts were dried
  3. temperatureheated on a steam bath for 1 h
  4. customevaporated
  5. temperatureThe residue was heated in benzyl alcohol (21 ml) at 100° for 18 h
  6. distillationThe mixture was then distilled in vacuo
  7. custompurified by FCC

Sources & evidence

ORD record
ord-36566ce6cd8b477a89f24a8bd4f63471
Source dataset
uspto-grants-1991_06
Patent number
US05023378

Reaction notes

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